Entrepreneurship Program Manager, Founders School - $200,000​/year USD

Traditional high schools define achievement by test scores and grade point averages. At Founders School, achievement means launching real businesses, solving tangible problems, and enabling students to reach outcomes most adults would view as unattainable.

We need someone capable of inspiring, pushing, and mentoring driven teenage entrepreneurs as they create functioning companies, harness artificial intelligence, and work toward ambitions typically reserved for adulthood.

If high expectations, complete ownership, and guiding remarkable young people toward exceptional results excite you, continue reading.

• Sustain daily execution and forward momentum across your assigned student cohort via standups, coaching conversations, and accountability frameworks.
• Lead weekly one-on-one coaching sessions and daily touchpoints that enable students to navigate challenges and sustain forward progress.
• Track student activity within FounderOS, catch signs of stagnation early, and mobilize support resources as needed.
• Facilitate connections between students and mentors, founders, operators, and opportunities that drive accelerated development.
• Design and deliver workshops, events, and community programming that reinforce culture and elevate performance expectations.
• Demonstrate hands-on AI application and guide students in integrating AI into their ventures, systems, and strategic thinking.
• Accompany students on 3-4 school trips annually.

• Offering in-depth strategic business advisory as students develop their ventures. That falls to FounderOS, Entrepreneurs-in-Residence, and visiting mentors.
• Tolerating work that does not reflect a student's established capabilities.
• Delivering academic instruction. The academic platform and its team manage that domain.
• Facilitating workshops beyond your proven competencies.
• Offering generic materials or connections that fail to align with Founders School quality standards.

Build the culture, accountability structures, and support infrastructure that empower ambitious student founders to execute reliably, use AI strategically, and reach outcomes that surpass what conventional education allows.

• 3+ years in leadership or high-impact individual contributor positions at startups, scaling companies, or equally rigorous settings.
• The capacity to participate meaningfully in entrepreneurial dialogue and recognize when specialized expertise is required.
• A standout competency beyond coaching: workshop design, event orchestration, content development, community cultivation, relationship architecture, or something similarly impactful.
• The presence to capture and hold the focus of driven teenagers and build an environment they are eager to join.
• The skill to communicate challenging feedback in ways that heighten drive and output.
• Regular application of AI tools with concrete demonstrations of how AI enhances your performance.
• Readiness to work on-site in New York City (relocation assistance available).
• Legal authorization to work in the United States.

• Launched or co-launched a company.
• Background coaching, guiding, or managing programs aimed at teenagers or emerging adults.
• A developed network of founders, operators, investors, or advisors.
• Early-phase startup exposure requiring you to assume diverse responsibilities and create processes from the ground up.

Founders School is a four-year high school built for ambitious students who want to create, build, and solve meaningful problems. The program combines Alpha School's elite academics, real-world experience, and mentorship from world-class entrepreneurs around three commitments to every student:
Build a million-dollar business. Identify problems in the world worth solving. Master AI before adults do.

This is a place for people who'd rather build the thing than manage the thing. We're hiring the founding team that builds the dream high school for the most entrepreneurial and ambitious students in the country. Launching in NYC Fall 2026.

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult  for more details on this topic.